Apart from socks that slide down, having a dress shirt that comes untucked constantly is one of the most annoying things in menswear. Today, we reveal the most important aspect of keeping a shirt tucked in all day.

You don’t want to tuck in your shirt 4 times a day at the office or even worse, having your shirt coming untucked during a meeting.

Some people come up with interesting techniques such as the military tuck which actually just helps to prevent the look of too much excess fabric on the sides if you get a shirt that is too wide. Or you can have the underwear tuck but ultimately, it’s not going to help you because the cause is actually a different one.

No, I’m not talking about shirt garters / shirt stays, you’ve watched different videos, you’ve probably seen them, little garters that are connected to your socks and they basically pull down your shirt when you move it up but ultimately, it’s just trying to fix the results of something, it does not go to the root cause.

Common Shirt Stays or Garters

Let’s compare the shirt getting untucked to a dripping faucet. You can either just put a little bucket underneath of it, or you can turn off the water of the main line every time you want to use it, or you can simply fix the faucet so it doesn’t drip anymore.Using sock and shirt garters or tucking in your shirt a certain way is the equivalent of putting a bucket underneath the dripping faucet.

Dress shirts are traditionally longer in the back and in the front but shorter on the sides

The biggest secret to getting a shirt that stays tucked in all day is to have a shirt that fits you properly. More specifically, you have to look at the following things.

1. Get Long Shirt Tails

Dress shirts are traditionally longer in the back and in the front but shorter on the sides so there’s not too much excess fabric. I suggest that the rear of your shirt covers your bum and has a same length on the front, that way, it won’t become untucked no matter if you wear your pants or your trousers on your natural waistline or lower on your hips.

The perfect fit will not constrict movement

2. Small Tight Armholes

The proper fit of an armhole is relatively tight; that means there’s not much excess fabric around your armpit and your shoulders. It fits very close. Now, most people think, when something is smaller, it is less comfortable, but in this case, it’s the opposite.

When I have a small armhole and I move up my shirt, the bottom part doesn’t move because nothing pulls on it. Let’s assume my armhole is slightly bigger, now the minute I pull up my arm, everything is pulled up and becomes untucked. The second I go down again, I have excess fabric being undone above my waistband.

A great fitting shirt will allow you to move around without getting untucked

Basically, whenever you buy a dress shirt, you should try it on and make sure that the armholes are as small as possible while still being comfortable. So if you have shirt and sock garters, they may pull the shirt back in but it’s not always perfect because once it has been pulled out, something may get caught and you can’t pull it right back in. Also if you have a thinner fabric, it shows in your pants. Let’s assume you’re on a date and you get to the crucial part and you have to take off something as ridiculous as your sock shirt garters; not only is that really unattractive but it may also kill the mood.

On the other hand, if you have a small armhole, you can move around, you can wave for a cab, you can say hi, you can shake hands, you can sit down, and your shirt will be tucked in all day and you won’t have to worry about it. Now of course, if you go climbing in a dress shirt, or if you workout, it will come untucked eventually but dress shirts are not meant for these kinds of activities and if you want to do something physical, get a t-shirt that’s flexible or a polo shirt.

A little bit of excess fabric goes a long way

3. Sleeves That Have Enough Room

Right now, it’s very popular to have slim sleeves and that’s okay but you should always make sure to have a little bit of fabric in the top part around your biceps because the minute you move forward or up, you need that extra room so your shirt does not come untucked. If it’s super tight, you are more likely to pull out your shirt by moving your arms around. If your shirt body is wider or slimmer, will it have a huge impact on the fact where it comes untucked or not? If it’s super wide, it may come untucked a little easier and you’ll also have more fabric hanging around in the first place. So if you don’t like your shirts coming untucked, try to get a trimmer fit that is based on your body. Avoid something that’s overly tight or you’ll get x-wrinkles because that’s unflattering as well.

If your shirt body is wider or slimmer, will it have a huge impact on the fact where it comes untucked or not? If it’s super wide, it may come untucked a little easier and you’ll also have more fabric hanging around in the first place. So if you don’t like your shirts coming untucked, try to get a trimmer fit that is based on your body. Avoid something that’s overly tight or you’ll get x-wrinkles because that’s unflattering as well.

wrinkling is definitely a sign of an improper fitting shirt

For classic evening shirts, back in the day, men wore a bib insert that was either starched or Marcella. They were quite stiff and so when people would sit or dance, they needed a little latch on the shirt that was able to be buttoned into the pants and that way, it would not move at all, all night. Unlike shirt garters, you can easily undo that very quickly, you don’t notice it and it really serves the proper purpose of not having your shirt come undone or move around because it’s connected to the pants. Again, for regular dress shirts, this is not necessary but it’s something specifically designed for evening shirts.

If you have a body that’s symmetrical or if you have issues with getting your shirt untucked, I suggest you invest in a custom shirt because you can really make sure that you get a tight armhole, that you can get a fitted shirt and you get the extra amount in your sleeve that is not too wide and that way, you’ll have a shirt that looks good on you, that flatters you, and won’t come untucked.

Still Thinking You Need Shirt Stays? Get these

Now, if you want shirt stays for nostalgic, vintage loving reasons or if you have a bunch of shirts with armholes that are too big but you cannot replace them at the moment, take a look at these shirts stays from sharp & dapper. Unlike most, they attach to your shirt at 3 points and they are more comfortable when you sit, even though we think nothing is as comfortable as a well-fitting custom shirt with tight armholes and no shirt stays or sock suspenders.

Some years ago I was told by the shirtmaker at Dunhills in London that the best way to secure the fit of a shirt was, after one was dressed, to put a hand (ones own) into the open trouser fly, to grab the bottom front end of the shirt on one side and to give it a firm tug down, and then to do the same with the shirt front on the other side. Sounds odd, but it works .. at least for custom made Dunhill shirts.

I tend to pull my shirt back down into my trousers by grabbing it and pulling down with my hands in my pockets – I find this works and looks better during the day than trying to stuff it back down past your belt

I see the problem is once the shirt is pulled out of the waist band it ain’t going back in. Perhaps a looser fitting waist band where the shirt can drop back down. Now to keep the pants from dropping at the wrong time, wear braces. Not sure if this would work 100% as the braces could cause the shirt to collect under them, stopping the shirt from returning to its proper place. My other weird idea is to attach the shirt to the elastic waist of the underwear. Hassle if you have to go to the mens room and could cause slight pain if you bent over too far. And women think we men have it easy!

Love your videos and I ask you to please please do one on (A) wearing the right size pant waist and (B) what it looks like when you don’t not to mention it makes your “pot belly” look larger and you heavier.

Thank you so much……I registered all the men in my family as recipients of your newsletter.

PS who checks you before your videos or during them? Check out your tie in the shirt video. Just a thought…during my past life, one of my tasks was to make sure my Chairman and CEO always appeared perfect on the videos…..credibility. Just a thought. You , 99% of the time DO!!!! Picky I know but you are all about PERFECT!!!!!

Hi Sven and all Gentlemen who follows the Gazette, Sorry for the late reply but other life priorities take precedence sometimes. I normally read and watch the Gazette for general knowledge and self style improvement. On this topic, I felt inclined to share my experience. Not so much about experiencing the “undone” or “untucked” shirt but more so the “mushroom” effect. For the gents who are unfamiliar with the term, this is when the shirt bulges out from the back like the mushroom discs spawning on tree trunks! As the vast majority of men, this is so common that colleagues and fellow gents almost except this fact as normal and have trained their eyes to ignore it as if it is invisible or just another normal fact of life. Nevertheless, the problem is there for the aware dappers. The problem always occurs when one is at a sitting position such as working at a desk and stands up afterwards. The long fabric part at the back of the shirt slips up from under the pant or waistcoat of a suit as in my case to accomodate the bend in the body position while sitting and when you straighten up at a standing position the excess fabric that was doing a great job covering your back and making sure your underwear is not showing becomes a burden and a sore to the eye! This lead me to relentless search for a solution which as Sven mentioned is not in shirt stays attached to the socks (being single band or tri-band). Underwear tucks makes the situation worse and strings … ?!? Finally, I came across a concept developed by a gent who had enough of this problem and decided to do something about it (good for him and all of us). His idea is a shirt stay of course but instead of hooking it up to your socks and risk loosing a date when you make it to the bedroom, it is simply attached to a band around your thigh. Each band has 3 straps to hold the shirt from the front, side and back virtually rendering it untuck-proof. The design is visually acceptable and not taxing on the eye should your date gets to the part of seeing it. What’s more, it is custom made to the measure of your thigh circumference and the straps are length adjustable to suit all body heights. And finally, it is available in 3 colours black, navy and tan or beige to avoid detection through lighter fabric! Please note that I am not running an ad to this company or its product nor I have any affiliation with it or its owner. The product is on Kickstarter and it has surpassed its funding target which says something about the product. Last email I received yesterday informed me that there are 3 days left till the funding period is over. Contributing towards a predetermined fund packages will buy you this product or multiple quantities of it at a discounted price from what it will be selling later on on their website. If you are interested even for looking it up, check out the S-Holder product by NV on Kickstarter. I cannot say yet if this product will surely resolve the long standing problem of untucked shirts until I give it a try. However, it looks as though it has the potential to do so. You may judge for yourself and be kind enough to share with us your opinion on this blog. Also, I would like to know what Sven think of it as a newly added necessity for the gentlemen wardrobe. Thank you for reading.